2-Methyl-2-(3-nitrophenyl)propanenitrile → 2-(3-Aminophenyl)-2-methylpropanenitrile

HRID 1667845Notes

Reaction equation

HRID 1667845 reaction equation
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-])=O)[CH:7]=1)([CH3:5])[C:3]#[N:4]>C(OCC)(=O)C.[Pd]>[NH2:12][C:8]1[CH:7]=[C:6]([C:2]([CH3:5])([CH3:1])[C:3]#[N:4])[CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 1

HCID 155413242-Methyl-2-(3-nitrophenyl)propanenitrile

Product 1

HCID 569657872-(3-Aminophenyl)-2-methylpropanenitrileYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-methyl-2-(3-nitrophenyl)propanenitrile (0.35 g, 1.8 mmol) in ethyl acetate (10 mL) was added 10% palladium/carbon (35 mg), and the mixture was stirred for 10 hr under hydrogen atmosphere. The residual catalyst was filtered through celite, and washed with ethyl acetate. The filtrate was concentrated under reduced pressure to give the title compound (0.35 g, 1.8 mmol) as a pale-yellow oil.

Workup

  1. filtrationThe residual catalyst was filtered through celite
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-36b644ffb6884dbb9103f3cd7fed1576
Source dataset
uspto-grants-2011_10
Patent number
US08044049B2

Reaction notes

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